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Matsubara T, Hayashi A, Banno Y, Morita T, Nozawa Y
Cerebroside of the dimorphic human pathogen, Candida albicans
Chemistry and Physics of Lipids 43(1) (1987)
1-12
Candida albicans 3125
(Ancestor NCBI TaxID 5476,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Organ / tissue: yeast,
mycelium
The structure was elucidated in this paperNCBI PubMed ID: 3555875Publication DOI: 10.1016/0009-3084(87)90012-0Journal NLM ID: 0067206Institutions: Department of Chemistry, Faculty of Science and Technology, Kinki University, Osaka, Japan, Department of Chemistry, Faculty of Science and Technology, Kinki University, Osaka, Japan, Department of Biochemistry, Gifu University School of Medicine, Gifu, Japan
Structural studies on the cerebroside isolated from the yeast form of a dimorphic pathogen, Candida albicans were carried out using fast atom bombardment mass spectrometry (FAB/MS), proton magnetic resonance spectrometry, gas chromatography-mass spectrometry and usual chemical methods. The component sugar was only glucose attached to ceramide in a beta-configuration. The major fatty acid was 2-hydroxystearic acid (62%). The predominant long chain base was identified as 9-methyl-C18-sphinga-4,8-dienine which is widely distributed in fungi and reported to be essential to the fruit-inducing activity of fungi. Therefore, the structure of the main molecular species of the cerebroside was determined to be N-2-hydroxystearoyl-1-O-beta-glucosyl-9-methyl-C18-sphinga-4,8-dienine. Cerebroside prepared from the mycelial form of C. albicans has the same structure.
glycolipid, Candida albicans, cerebroside, 9-methyl sphingadienine, branched long chain base, human pathogen
Structure type: monomer ; 754 [M-H]-
C
43H
80NO
9Location inside paper: p.8, p.10, fig.7, GL-1
Compound class: glycosphingolipid, cerebroside, ceramide
Contained glycoepitopes: IEDB_137339,IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_5
Methods: 1H NMR, methylation, IR, FAB-MS, GC-MS, TLC, acid hydrolysis, GLC, methanolysis, extraction, periodate oxidation, reduction, column chromatography, cell growth, derivatization, glycolipid detection, osmium tetroxide oxidation
Comments, role: no significant change occurs in glycolipid composition during the yeast-mycelial conversion of C. albicans
Related record ID(s): 40549, 40812, 40813, 40814, 42250, 42251, 42252, 42253, 42254, 42256, 42257, 42258, 42259, 42260, 42261, 42262, 42263, 42264, 42265, 42266, 42267, 42268, 42269, 42270, 42271, 42272, 42273, 42274, 42275, 42276, 42279, 42280, 42281, 42282, 42287, 42288, 43402, 43403, 43418, 43419, 43420, 43672, 43673, 43674, 43679, 43680, 43704
NCBI Taxonomy refs (TaxIDs): 5476
Show glycosyltransferases
NMR conditions: in vol 90%CHCl3 / vol 10%CH3COOH at 293(H) K
[as TSV]
1H NMR data: present in publication
|
There is only one chemically distinct structure:
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Matsubara T, Hayashi A, Banno Y, Morita T, Nozawa Y
Cerebroside of the dimorphic human pathogen, Candida albicans
Chemistry and Physics of Lipids 43(1) (1987)
1-12
Candida albicans 3125
(Ancestor NCBI TaxID 5476,
species name lookup)
Taxonomic group: fungi / Ascomycota
(Phylum: Ascomycota)
Organ / tissue: mycelium
The structure was elucidated in this paperNCBI PubMed ID: 3555875Publication DOI: 10.1016/0009-3084(87)90012-0Journal NLM ID: 0067206Institutions: Department of Chemistry, Faculty of Science and Technology, Kinki University, Osaka, Japan, Department of Chemistry, Faculty of Science and Technology, Kinki University, Osaka, Japan, Department of Biochemistry, Gifu University School of Medicine, Gifu, Japan
Structural studies on the cerebroside isolated from the yeast form of a dimorphic pathogen, Candida albicans were carried out using fast atom bombardment mass spectrometry (FAB/MS), proton magnetic resonance spectrometry, gas chromatography-mass spectrometry and usual chemical methods. The component sugar was only glucose attached to ceramide in a beta-configuration. The major fatty acid was 2-hydroxystearic acid (62%). The predominant long chain base was identified as 9-methyl-C18-sphinga-4,8-dienine which is widely distributed in fungi and reported to be essential to the fruit-inducing activity of fungi. Therefore, the structure of the main molecular species of the cerebroside was determined to be N-2-hydroxystearoyl-1-O-beta-glucosyl-9-methyl-C18-sphinga-4,8-dienine. Cerebroside prepared from the mycelial form of C. albicans has the same structure.
glycolipid, Candida albicans, cerebroside, 9-methyl sphingadienine, branched long chain base, human pathogen
Structure type: monomer ; 754 [M-H]-
Location inside paper: Fig.7, GL-1
Compound class: glycosphingolipid, cerebroside
Contained glycoepitopes: IEDB_137339,IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_5
Methods: 1H NMR, methylation, IR, FAB-MS, GC-MS, TLC, acid hydrolysis, GLC, methanolysis, extraction, periodate oxidation, reduction, column chromatography, cell growth, derivatization, glycolipid detection, osmium tetroxide oxidation
NCBI Taxonomy refs (TaxIDs): 5476
Show glycosyltransferases
NMR conditions: in 90%CDCl3 / 10%CD3OD at 298(H) K
[as TSV]
1H NMR data: present in publication
|
There is only one chemically distinct structure:
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Kawai G, Ikeda Y
Chemistry and functional moiety of a fruiting-inducing cerebroside in Schizophyllum commune
Biochimica et Biophysica Acta: Lipids and Lipid Metabolism 754(3) (1983)
243-248
Schizophyllum commune IFO 6502
(Ancestor NCBI TaxID 5334,
species name lookup)
Taxonomic group: fungi / Basidiomycota
(Phylum: Basidiomycota)
The structure was elucidated in this paperPublication DOI: 10.1016/0005-2760(83)90138-8Journal NLM ID: 0217513Publisher: Elsevier
Institutions: Noda Institute for Scientific Research, Noda-shi, Japan, Nodai Research Institute, The Tokyo University of Agriculture, Tokyo, Japan
A cerebroside prepared from Schizophyllum commune and shown to have fruiting-inducing activity on the same fungus was studied chemically and biologically. Chemical degradation, which was followed by extensive applications of nuclear magnetic resonance and mass spectrometry to the derivatives, suggested a structure (4E,8E)-N-D-2’-hydroxypalmitoyl-1-O-β-D-glucopyranosyl-9-methyl-4,8-sphingadienine. The degradation products and the derivatives were submitted to a fruiting-inducing assay. The reduced periodate-oxidized cerebroside and the ceramide were as active as the original cerebroside, but the hydrogenated cerebroside and the hydrogenated ceramide were less active and the N-acetyl and N,O-acetyl sphingoids were much less active. The glycoside, the fatty acid, the psychosine, the sphingoid, the acetonide of the N-acetyl sphingoid, and the dinitrophenyl derivative of the hydrogenated sphingoid exhibited no activity. It was concluded that both the methyl branch of the sphingoid and the acid amide linkage in the cerebroside may be the functional structures of the fruiting-inducing substance.
lipid structure, cerebroside, Schizophyllum commune, fruiting induction
Structure type: monomer
C
41H
77O
9N
Location inside paper: Fig.1
Trivial name: cerebroside B
Compound class: glycolipid, glycosphingolipid, glycoside, cerebroside
Contained glycoepitopes: IEDB_137339,IEDB_142488,IEDB_146664,IEDB_983931,SB_192,SB_5
Methods: 13C NMR, 1H NMR, IR, acid hydrolysis, GLC, HPLC, alkaline hydrolysis, enzymatic digestion, extraction, periodate oxidation, optical rotation measurement, acetylation, reduction, column chromatography, cell growth, derivatization, osmium tetroxide oxidation, hydrogenation
Biological activity: Cerebroside exhibits fruiting-inducing activity on Schizophyllum commune.
NCBI Taxonomy refs (TaxIDs): 5334
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There is only one chemically distinct structure:
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